


A Little Ditty about Jeff and Diane

by Janeway578



Category: Political RPF - US 20th c., Political RPF - US 21st c.
Genre: F/M, Roleplay
Language: English
Status: In-Progress
Published: 2017-03-15
Updated: 2017-09-03
Packaged: 2018-10-05 08:23:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 6,826
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10302197
Author URL: https://archiveofourown.org/users/Janeway578/pseuds/Janeway578
Summary: Strangers in the Night





	1. A Little Ditty About Jeff and Diane

"From the gentleman in the corner."

The woman at the end of the bar looked up as the tumbler of scotch was placed in front of her by the scruffy bartender.

Tucking her bobbed red hair behind her ear, she held up the glass toward the darkened corner, meeting the eyes of a middle aged man sitting alone at a table there. He smiled briefly and returned the gesture, then went back to the newspaper he seemed to be engrossed in. Well, this was intriguing. She had thought for sure that he was going to demand at least a banal conversation in return for his $10 investment, but to her surprise, he seemed uninterested.

The scotch was smoky and she allowed it to swirl in her mouth for a second before it slid down her throat. Soon, she found her eyes drawn to her benefactor again, free to roam unhindered by his stare. He looked mid-fiftyish with thick, wavy hair, graying at the temples. He had taken his sport coat off and rolled up the sleeves of his light blue dress shirt, and she noticed muscular forearms and lean wrists that led to large hands and long, slender fingers. His forehead was furrowed in concentration and she couldn't quite make out his eyes, but she could see he had an oval-shaped face with a large, prominent nose and a strong jaw. Oh my, he was a good looking man, she admitted to herself.

She licked her lips unconsciously and caught her bottom lip between her teeth and as if he could feel her eyes on him, he looked up. Shit, she was caught. He quirked a brow and she smiled sheepishly. Already almost 2 scotches deep, she felt the liquid courage pulsing in her veins and decided to take the plunge and introduce herself. Glass in hand, she sauntered toward him, making sure to add just the right amount of sway to her hips as she did. His eyes never left hers.

"I figured if I'm going to keep getting caught looking at you, I should probably introduce myself. I'm Diane," she said, extending her hand in greeting.

He chuckled. "Jeff. Nice to meet you Diane." He shook her hand and held on just a fraction too long.

"Thank you for the drink, Jeff."

He gestured for her to sit and she took the seat across from him at the little table, leg brushing his as she pushed her chair in. She wondered if the heat she felt in her cheeks could be blamed on the scotch or the proximity of the man. Either way, it left her feeling a bit giddy.

"My pleasure," he drawled, voice soft and rich like velvet.

"If you don't mind my asking, what brings you out on a Wednesday evening?" He asked.

She smiled demurely. "They have a great jazz band on Wednesdays," she said. "You're in for a treat if you plan to stay a while."

"Do you plan to stay a while, Diane?" His eyes seemed to implore her.

"Yes," she said simply.

"Then so do I."

Her eyes held his as she swirled her finger around the rim of her glass then brought it to her lips, eliciting an almost imperceptible intake of breath from her companion.

"And what brings YOU out on a Wednesday evening?"

He tried once to answer but his voice seemed to fail him and he had to clear his throat.

"Well, I'm here from out of town, been in seminars all day. I thought it would be nice to unwind with a drink after a long day. Some of my peers were supposed to meet me here, but it appears I've been stood up."

"Lucky me," she replied, smiling seductively.

"What is it that you do?" She feigned interest. Honestly, she was just trying to distract herself from staring at his hands as they tapped a slow rhythm on the tabletop.

"Cardiologist at Providence," he answered.

"Oh, a mender of broken hearts, huh? Are you a breaker of hearts too?" Oh God, did those words really just come out of her mouth? What on earth was she doing?

He seemed to find her charming though, and despite her cheesy flirting, he chuckled.

As if the spirits had heard her prayer to end the conversation, the band chose that moment to begin their set, starting appropriately with 'You Go to my Head'. The piano dissolved and the pretty young singer stepped up to the mic:

 

_You go to my head_   
_You linger like a haunting refrain_   
_And I find you spinning round_   
_In my brain_   
_Like the bubbles in a glass of champagne_   
_You go to my head_

 

He held his hand out to her and she slid into his arms on the tiny dance floor.

 

_You go to my head_   
_Like a sip of sparkling burgundy brew_   
_And I find the very mention of you_   
_Like the kicker in a julep or two_   
_The thrill of the thought_   
_That you might give a thought_   
_To my plea, casts a spell over me_

 

Their joined hands rested against his chest and their cheeks were so close together that she could feel his evening stubble against her face. The heady scent of his cologne filled her senses. Their movements were slow, sensual, deliberate.

 

_Still I say to myself_   
_Get ahold of yourself_   
_Can't you see that it never can be_   
_You go to my head with a smile_   
_That makes my temperature rise_   
_Like a summer with a thousand Julys_   
_You intoxicate my soul with your eyes_   
_Though I'm certain that this heart of mine_   
_Hasn't a ghost of a chance_   
_In this crazy romance_   
_You go to my head, you go to my head_

 

As the piano player faded on the refrain, he immediately went into Davis's 'Blue in Green' and the singer moved away to make room for the trumpet player at center stage.

The first wail of the instrument hit her and she moved her cheek gradually closer to his. In turn, his hand at the small of her back pressed her tighter against him, heat branding her so that she had to suck in a breath to steady herself.

Every note of the song was slicing through her and she found herself turning her head toward him, lips grazing the side of his neck and feeling the pulse there.

He slowly untangled their hands and reached into his shirt pocket, and a moment later she felt something flat and rectangular being pressed into her palm. His room key.

"Yes," she whispered close to his ear, and he pulled away a bit to look in her eyes. She held his gaze and gave a small nod to confirm her acquiescence.

He nodded in return, then brushed his fingers over her cheek and without another word, walked away, daring her to follow him. The ball was in her court.

She was stalk-still a moment before desire and intrigue propelled her forward and she practically ran to catch up to him.

They walked side by side through the hotel lobby, not touching, not speaking, each of them afraid the spell would be broken if even a word was uttered. She watched the lights of the elevator 5, 4, 3, 2, as it made its way down to the ground floor slowly, agonizingly slowly.

Finally the doors opened and admitted them entrance and they stepped in, shoulder to shoulder. Like a shot she was on him as the doors closed, wrapping her arms around his neck and pulling his head down to hers to join their lips in a heated kiss, which he returned with fervor. Lips, tongues and teeth sliding against each other in a seductive duel.

Her back landed against the mirrored wall with a soft thud, and through their haze they barely heard the ding of the elevator signaling their arrival to his floor. They pulled apart like lightning and he took her hand to lead her to his room, walking briskly down the hallway.

He pressed into her, his front to her back as she inserted the key into the lock and she could feel him shudder as the door clicked open.

He pushed them inside and the moment the door closed he backed her up against it, hot breath on her neck and hands that seemed to be everywhere.

"I just want you to know," he said between nips to her skin, "I don't ever do this sort of thing." He moaned as she unbuckled his belt and unfastened his pants with a speed and dexterity he didn't think possible.

She stopped her movements to look him in the eye.

"Me either. One night stands aren't usually my forte, but God I'm attracted to you."

Lips colliding, she had his pants and boxers around his ankles in seconds and he stepped out of them, still clad in his dress shirt which was now tented with his growing erection. In turn, he grabbed the sides of her shirt and pulled hard enough to pop the buttons off and she moaned into his mouth as his hands covered her breasts.

She moved away and took a moment to rid herself of her shirt, skirt and panties then pushed him toward the small ensuite bathroom where she hopped on the counter and pulled him between her parted thighs. She wrapped her stocking-clad legs around his waist but when she attempted to remove her black stiletto pumps, he stopped her.

"Leave them on," he pleaded, so she did.

One hand on the mirror behind her and the other at the small of her back, he shifted her to the edge of the counter and she wriggled until he was lined up at her entrance. Foreplay was unnecessary; if he wasn't inside her soon she would scream.

He pushed inside and they both took a moment to adjust before he began moving in earnest. She was perched on her hands and used them to counter his thrusts, her head hitting the mirror in time with each one.

"You feel good," he whispered.

"So do you," was her husky reply.

He changed the angle and quickened the pace until they were both moaning, and she could feel the first stirrings of orgasm coming alive within her.

"I'm close," she whimpered.

He took that as an opportunity touch her center, and he immediately felt the hard clench of her inner muscles as she started to come.

"Ohhhhh God," she groaned, the spasms seemingly unending.

Feeling her come apart all around him triggered his own release and he pulled her to him as he collapsed against her, both panting.

When they caught their breath, he lifted her gently from the counter and she followed him into the bedroom, bed still made from earlier in the day. He turned down the sheets and then turned to look at her, still undressed from their coupling and unabashedly sexy.

"I hope you'll stay," he said sincerely, and she found she truly wanted to.

She nodded and climbed under the covers beside him, allowing him to wrap his arms around her from behind as they both fell blissfully to sleep.

 

*******

The bed was unfamiliar but the soft breathing behind her soothed Hillary's soul, as it had for decades.

She felt Bill beginning to stir and rolled over to trace his face with her fingertips. Paying special attention to his lips, she smoothed her thumb over them and when that didn't illicit a response, she kissed him softly on the mouth. His eyes fluttered open and he smiled, bringing his hand around to tuck her blonde hair behind her ear.

"Sleep well, Honey?" She asked with a hint of mischief in her tone.

"You know I did," he chuckled.

She kissed him again and moved her lips to his ear.

"You were amazing last night Jeff," she whispered.

He laughed outright. "I'm so glad I met you Diane."

They lay quiet a minute, and then:

"Oh and Hilly, don't you dare get rid of that wig!"

Her squeal of laughter could be heard as he pulled the covers up over their heads and began to ravish her anew.


	2. Walk on the Wild Side

His phone buzzes where it sits on the desk. "Hi, this is Diane from the agency. I'm in the lobby downstairs, on my way up."

He pops a bottle of champagne and loosens his tie.

A few moments later, a knock at the door. She walks in all in black except the shiny deep red of her lips. She wears a lace sheath dress with a sheer overlay at the chest, falling just above her knee. Sheer black stockings lead down shapely legs to impossibly high heeled pumps. Honey blonde hair swept into a loose chignon, smoky yet elegant eye makeup, diamonds dripping from the lobes of her ears. She extends a delicate hand in his direction.

"Hi I'm Diane."

"Jeff," he says as he wraps his fingers around hers.

"Pleasure to meet you Jeff," she purrs through those ruby red lips.

"I settled your fee with the agency," he says.

She smiles seductively. "I take it you know what you want then? I like that in a man."

"Have some champagne," he says, pouring her a flute and pressing it into her hand. She takes a sip and wets her lips.

He moves the chair from the desk to the center of the room, then takes a seat and begins to take off his tie. 

"May I?" she asks, creeping closer.

His eyes darken. "Take your dress off for me first, I want to watch you," he commands.

"Whatever you want Sugar," she coos. "But I'll need a little help with this zipper." 

She turns around and he steps up behind her to slowly unzip the back, then sits down again.

"Turn around and strip for me."

She locks eyes with him as she slowly slides one slender arm out of her dress.

"Move your hips darlin'," he drawls. Her hips sway sensually as the dress slips down her other arm. He licks his lips.

"Sexy." His voice is rough like wool.

"Thank you Honey."

"Take it all the way off," he pleads.

She pushes the dress over her rocking hips and lets it cascade to the floor in a pool around her feet. She steps out of it, leaving her in a black satin corset attached by thin garters to her lace-topped stockings. 

"Turn around for me." 

She does a slow turn and hears his sharp intake of breath. The laces of the corset end just above where the thin sliver of lace disappears between the cheeks of her ass. "Fuck," he whispers.

"I want you to take off my clothes," he says.

She saunters over to where he's sitting and slowly lowers herself to her knees in front of him, sliding the knot out of his tie then pulling it off with a flourish. Small fingers slip each button of his dress shirt through the holes, trailing down the bare skin of his chest as it's revealed. She gazes up at him from under incredibly thick black lashes.

"Mmmm that's it," he says.

She helps him take the shirt all the way off and it drops to the floor.

"Better Sugar?" He nods.

"You want to take off your pants and show me what you got in there?" she asks huskily. Soon he's naked except for his black dress socks, cock jutting up hard and proud from between his legs. He takes it in his hand and pulls it toward her, as if in offering.

"Put your mouth on me." He's getting into it now, she can see the precum oozing from the slit.

"Yeah? You want me to suck your cock Honey? Wrap these lips around you?" His nostrils flare as he nods.

"Relax Sugar, I'll be so good to you."

She spreads his legs apart and moves further between them, bending over to swirl her tongue around the head of his cock before engulfing his entire length in her mouth. She relaxes her throat muscles to take him deeper while moving one hand to wrap around the base, then she sucks all the way back up greedily. 

"Fuck," he says again.

He grabs the back of her head and uses a gentle hold on her hair to guide her movements. She's so good, he's fucking her expert mouth without restraint after a few short minutes. She hums around him and he flexes his thigh muscles. His balls are tightening and she knows he's getting close so she backs off so he doesn't come in her mouth. 

"Finish me with your hand," he whispers desperately, loosening his grip on her hair so she can move her face away. She continues the frantic pace with her hand wrapped snugly around him until he throws his head back and shoots off in her palm.  


"Yessss," he hisses.

She continues to pump him softly until the sensitivity becomes to much for him and he stills her hand with his own, warm and soft against hers. 

"May I clean you up?" she asks. 

"There's towels in the bathroom." She returns, wiping her hands on the hand towel, then proceeds to gently clean the spend from his groin and thighs.

"I want to fuck you," he says matter of factly.

"Anything you want, just no bareback," she replies. Her voice oozes sex and seduction and promises of untold pleasures.

"I need a few minutes. You can touch yourself while I watch. Against the wall there, panties off." His eyes are hard, demanding, authoritative.

She does as he says and backs up against the wall between the bed, wet center exposed, and leans her head back into it, trailing one hand down between her corseted breasts to the heat between her thighs. He moves to sit on the bed directly in front of her, watching her with dark eyes.

She dips her middle finger into her abundant moisture then drags it up her slit to the hood of her clitoris. She uses two fingers of her other hand to spread herself wider and adjusts her stance so he can see her intimate movements. Circling her clit slowly, she lets out a breath which ends in a whimper. Her eyes stay on him, she can see she's having an effect on him. He's beginning to stroke himself in time to her movements, not hard yet but starting to get there.

She's lost in her own sensations now, enjoying the feelings her fingers are eliciting. Her whimpers are genuine, jolts of pleasure shooting through her with each circle to her engorged nub. She barely registers his movement until her leg is thrown over his shoulder and his mouth quickly and forcefully takes over for her fingers. 

"Mmmm, you want to play too Sugar?"

He nods and attacks her clit with his tongue while sinking 2 fingers into her sodden depths. She sucks in a breath. He's good. 

"You want to come?" he pulls away and asks.

"That's up to you Honey, it's your dime," she rasps. She's not sure she could stop herself from coming at this point even if she tried.

He gives a final lick to her bud and then stands up and turns her around roughly to face the wall. Her hands go out to steady herself as he runs his down her back and around her waist to lift her hips. She's not sure when he got the condom but she can hear him opening the package with his teeth and feel his dick rub against her ass as he rolls it on. Two fingers inside her again to ready her (as if she needs it) and then he's plunging into her hard to the hilt. He grunts like an animal next to her ear each time he slams back in and she pushes back against him in a deliciously hard counter measure. His hands rest beside hers on the wall.

"Tell me you like it," he orders.

"Feels so good Sugar," she coos. 

"No, say my name." A throaty plea.

"You feel fucking fantastic Jeff," she mewls. And she means it.

"You're so tight," he breaths.

"I'm so full of your huge cock." Not a lie.

"I want to feel you come around me," he pants, sliding his hand down around her and seeking out her clit, pressing then circling with precision.

"Jeff," she hisses.

"Come on," he commands. 

His balls are slapping against her ass with each thrust and his fingers are driving her insane and time slows and speeds up simultaneously. And then she stiffens and gasps, coming in waves around him. He shatters behind her a split second later, hips jerking rhythmically as he empties himself. He pushes them both heavily against the wall as he slips out of her with a groan. 

She stays where she is, palms flat on the wall as she gets herself together.

"How much to stay the night?" he asks softly from the other side of the bed.

She turns around and smiles. "I think we can work something out."

*****  
Another morning, another hotel. Secretary Clinton stretches and kicks off the covers, ready to get to the day's events. A hand on her wrist pulls her back into bed and a pair of soft warm lips captures her own.

"Good Morning Madame Secretary," Bill drawls.

"Mr. President," Hillary replies. 

"What would the people think if they knew their dear sweet Secretary of State turned into Dirty Diane, the high priced call girl by night?" he asks.

"Probably the same thing they'd think if they knew their 42nd President is Jeff who solicits high priced call girls to his hotel. And that he likes to give them as much pleasure as they give him."

She kisses him again with her sweet luscious mouth.  
"Nice touch not kissing on the mouth last night. Authentic," he laughs. 

"I'm going to assume you learned that from Pretty Woman and not from some other source," she chuckles.

He lifts up on his elbow in bed as she gets up to start getting ready.

"It was a pleasure doing business with you Diane," he says.

She stops and looks at him with hunger in her eyes. "The pleasure was definitely all mine, SUGAR." 

She crawls back into bed and pushes him over with a kiss. The day can wait a little longer.

Finished


	3. Bobby Sox to Stockings

**Summary for the Chapter:**

> [](https://www.flickr.com/photos/98007576@N00/37010284175/in/dateposted-public/)   
> 

**Notes for the Chapter:**

> I just want to reiterate that this series consists of two married, consenting adults ROLE PLAYING, in this case as 1950s teenagers. If anything they might do under that guise is offensive to you, please PLEASE stop reading. Or at least, don't be surprised at what you might read.
> 
> That being said, this was inspired by the above photo from Bill's 46th Birthday.

August 19, 1992

 

Fiddling with the newly placed pin on her lapel, she gazed out the windshield over the twinkling lights of the city below, a veritable patchwork of oranges and yellows.  Next to her, he shifted closer in the backseat.

She pulled something out of her purse and handed it to him.  “Here, I swiped this from the old man’s liquor cabinet.  Want some?”

“Naughty, aren’t we?” he said with a wink.  He unscrewed the flask and took a long drink, wincing as the alcohol hit the back of his throat and burned pleasantly down his esophagus.  The warmth surged through his veins and he smiled.  He handed it to her and watched her do the same.

“What is this stuff?” he asked, taking the little container back from her and tipping it to his mouth again.  Warmer this time, he could feel it in his cheeks now.  

“Bourbon.”  She took another pull and leaned back against the headrest, a dreamy smile on her face.

“It’s so pretty up here,” she sighed.  A pleasant buzz had enveloped her, both from the liquor and the company.

“I think _you’re_ so pretty Diane,” he responded.  He reached an arm around her and pulled her even closer against him, tilting her chin in his direction.  She swallowed hard and licked her lips in anticipation.  

“Can I kiss you?”  

“I don’t know, can you?” she asked playfully.  

His fingers held her chin as he brought his lips toward hers.  The kiss was light and sweet and he pulled back a moment later, searching her eyes for approval.

“That was nice.”  She relaxed into the crook of his arm.  “What should we do now?” she asked with a smile and an arched eyebrow.

He swung her legs over his and situated her so she was laying across his lap, then put his mouth to her ear and whispered, “We could neck for a while.”  

“I’ve got to be home by curfew.”  

“We’ve got plenty of time.  I just want to be close to you, don’t you want that too?”  

The look in his eyes had her melting.  “Yes.”

That was all the answer he needed.  He kissed her again, more demanding, tongue pushing gently against her lips to request entrance to her bourbon-laced mouth.  She opened for him, letting him slip it inside with a moan, then sucked greedily.

His hand went to her hair to untie the shiny ribbon around her blonde ponytail, loosening it so he could work his fingers into the silky tresses.  She shivered when the tips of his fingers massaged her scalp, a breathy little moan escaping the back of her throat.

Warm fingertips traced around the shell of her ear then trailed downward, over the pointed collar of her shirt, touching the newly placed pin and coming to rest against the top of her breast, which he cupped lightly before moving further to attempt to untuck her shirt.  She squirmed against him, suddenly nervous.

“Shhhh,” he cooed.  “It’s okay, I just want to feel your skin a little bit. I bet you’re so soft.”  

He held her eyes as he slipped his hand beneath her loosened shirt, up the warm skin of her abdomen and under the tightness of her cotton bra.  He shuddered at the feeling of her bare breast in his hand.  

“What is it?” she asked.

He squeezed her lightly and felt her nipple harden against his palm and knowing he was the cause of it shot a jolt of arousal straight to his groin.  His eyes closed and he savored it a moment, trying to will his body to calm down. 

“I really like touching you is all.  Do you like it?”

She pressed her chest further into his hand, a sign of encouragement.

“Yeah, mmmm” she rasped, then moaned when his thumb found her nipple and teased over it repeatedly.

“Do you want me to stop?” 

“No.”

“What do you want me to do?” he asked, voice strained.

“You could kiss me again, and keep doing what you’re doing here.”  Her voice was pleading.  His fingers on one of her most sensitive parts were making her feel tingly and wet between her legs.  Everything felt heightened and electric.

Their mouths met again, tongues finding each other’s easily.  He continued his ministrations on her breast but soon it wasn’t enough. He needed more of her. Without breaking the kiss, he pulled out of her bra and brought his hand down to the hem of her pink circle skirt and began to push it up her outer thigh.  She groaned and covered his hand with her own, easing out of their kiss.

“Jeff-”

“Come on Baby, please? Let me make you feel good. If you don’t like it I’ll stop-”

“Promise?” she breathed.

“Absolutely.”

Her hold loosened and he wasted no time skimming up her thigh, taking her skirt and petticoat with him until they bunched around her waist.  His hand slid between her knees and upward, slowly coaxing her legs apart, until he reached the apex of her thighs. Damp panties greeted his touch and he felt himself harden further at the sight of her, all pale and curvy and undeniably his.

“Relax Baby,” he whispered, leaning in to kiss her again as he began to rub her through the fabric.  She whimpered into his mouth and shifted her hips to meet him.

“Feel good?” he asked against her lips.

“Really good,” she said to him.  “Keep going.”

“Yeah?”

“Yeah. Please.”

His touch grew bolder, pulling her panties aside and letting just the tip of his middle finger dip inside, finding her hot and wet and slippery.  He dragged the digit between her  lower lips, watching her face for cues, noticing how her eyes rolled back and she exhaled quickly when he touched the small bundle at the top.

He did it again.  “Oh! My!”  she exclaimed.  She put her hand over his.

“Stop?”  

Her eyes were screwed tight, her breathing coming in warm puffs against his face.

“No,” she panted.  “I’ve just never felt like this before. It feels incredible. Keep touching me right there.”

He circled around her again, feeling the extra moisture created by his touch. Her hips started moving in tandem, and a steady stream of moans and whimpers poured from her lips as he continued.

“Ohhh...ohhhh....oh yessss...”  Her voice was getting higher and softer with each circular motion until finally she squeezed her thighs around his hand and stiffened, her body arching as pulses of pleasure rolled over her, from her center to the tips of her fingers and toes.  She collapsed against him a moment later, completely robbed of breath and coherent thought.

“You all right?”  He pushed a strand of hair off her forehead and behind her ear as he cradled her in his arms.

“Yeah...I,uh...gosh...”  She couldn’t form a sentence but she looked up at him, beaming.

“Should I take that as a compliment?” he asked her.

“Definitely.”  

He shifted uncomfortably beneath her and she could feel the hardness against her hip where their bodies were in contact.  She pressed more firmly into him and he squeezed his eyes shut, grabbing her to stop her movements.

“Baby,” he groaned.  

“Move over.”  She slid off his lap and sat next to him on the bench seat, resting one hand on his shoulder and grabbing a handful of his letterman sweater with the other.

She looked up at him, blue eyes innocent, and whispered, “Tell me what to do now.”  

“Will you touch it?” he pleaded, guiding her hand down to the bulge in his jeans.  “It’s so hard for you.”

Bottom lip between her teeth, her hands went for the button, undoing it and loosening his pants enough help him to slip them and his briefs over his hips then down his thighs.  His hard, thick erection sprang free, already dark and oozing from the slit.  She moaned at the sight of it, wide-eyed.

“Show me how you do it.”

He took her hand again, using his fingers to wrap hers around him and sliding their joined hands up and down the length of him, stopping to squeeze the sensitive head and spread the leaking moisture around it before stroking back down the shaft.

“That’s it,” he said softly.  “Don’t stop Baby.”

“It _is_ so hard,” she said with awe, watching as the tip moved in and out of her fist. “But the skin is so soft.  Can I kiss you there?”

He let his head fall back against the seat with a groan as she continued, her words making him even harder, if that were possible.

“Y-yes,” he stammered.  He was trying to maintain some semblance of control, but she was making it very difficult.

Holding him in her hand and bending toward him, she gave a tentative swipe of her tongue to the underside, like licking a sucker, then placed a soft kiss on the sensitive head.  He gathered her hair in his hands to push it away from her face so he could watch her, the first girl to ever bring him so much pleasure.

“Suck on it a little,” he begged.

She obliged and pulled him into her mouth, sucking gently.  The warmth and the wetness and the press of her tongue was driving him crazy - he didn’t know how much more he could take.

“Mmmmmm,” he moaned.   He stroked her hair as she took him a little deeper, closing her lips tightly around him and and pulling upward, stretching the skin, making him shudder.

“Stop,” he rasped.

“What’s wrong?” She eased off him and looked up, almost shy.  “Was it okay?”

“God, it was perfect, you were perfect.”  He wrapped his arm around her back and kissed her tenderly, his other hand cupping her soft cheek.

“I want to go all the way with you Diane.  Let me be the first, please?”

“Jeff-”

“But I love you.  I’m going to marry you someday. It’s right.”

She pursed her lips.  “I want you to be the first, but I’m afraid.”

“Tell me what you’re scared of.”

“It’s so big...” Her teeth sank into her plump bottom lip as her gaze drifted down between his legs.

“We’ll go slow Baby, as slow as you want.  Just the tip so it doesn’t hurt. Please, I need you so bad.” 

She nodded her acquiescence and he reached for the waistband of her pretty pink skirt, fumbling with the closures.  “Let’s get you out of this.”  His nervousness and excitement were clear by the waver in his voice and the trembling of his fingers.

“You’re shaking,” she said.

“I just want you so much,” he sighed.  “Want it to be special.”

She took over, unclasping and unzipping and slipping everything off, nylon and crinoline and lace hitting the floor of the backseat in a heap  When she was completely bare from the waist down she turned and cupped his cheeks as she threw a leg over his and sat astride him. Their naked flesh pressed together for the first time, his hardness against her soft wetness, and they groaned in response.

She kissed him and let instinct take over, rolling her hips gently against his, the tingling increasing between her thighs until she felt ready for him.

“Lift up Baby.” She shifted so she was hovering over him, watching as he took his straining erection in his hand.  He stroked it once before wrapping his fingers around the base, offering it to her.

“Get on,” he whispered.  She sank down and he pushed up until the tiniest bit of him was sheathed in her warmth.  Wincing momentarily, she let out a breath through her flaring nostrils, feeling the pleasant sting as her body accommodated his considerable size.

“I’m okay.”  She smiled and caressed his face.  “More.”

“Yeah?”

“Just go easy.”  Her hot breath fanned him.

They both watched, wrapt, as she accepted more of him, enveloping the entire thick head inside of her, pulling him deeper.

“Christ, you have no idea how good this feels,” he croaked.  “So snug around me, so soft like velvet.”

He eased in agonizingly slowly, further and further until he was buried all the way inside of her, every delicious inch of his cock surrounded by her tight heat.  She let out a soft whimper as he slid all the way home, burying her face in the crook of his neck to steady herself.

Eyes closed, he rested his hands on her hips to keep her still.  The way her walls had massaged his entire length had him already on edge and he hadn’t even moved yet.

“Damn.” He exhaled.  “You okay Baby?”

She pulled back to look at him. “Mmmmm yeah,” she murmured.  “I feel so full.”

In a valiant effort to keep his body under control, his hands went for the first button of her shirt, slipping it out of the hole and moving swiftly onto the second, then the third.  

“I want to see all of you,” he said.  “To touch all of you.”  The shirt fell away leaving her in only a bra on top of him, low light glinting off of her pale skin.  She reached behind her to unclasp it, letting it slide over her shoulders and down her arms, where he quickly discarded it.  

With shaky hands he reached out to touch her, letting her soft, supple breasts fill his palms, watching as her head fell back in pleasure.  He squeezed them together and her back arched, hips pushing against his slightly so he had to suck in a breath and let it out quickly.  By the time he leaned forward to run his tongue over one of her nipples she was mewling low in the back of her throat.  Her hips began to grind slowly on him, up and down, up and down,rubbing her sensitive bundle against his pelvic bone, coating him in her thick moisture.

“Oh Jeff,” she breathed.  “So good.  I love you so much.”

“Mmmmm, love you too,” he hummed around her nipple.  Arousal shot straight to her center and she bucked against him, clenching her inner muscles deliciously.  A guttural cry escaped his open mouth.

He moved his hands back down to her ass and gripped her firm cheeks, lifting her so she could slide up his length and then pushing her against his rolling hips on the way down to help stimulate her clit.  Her whimpers intensified and she pushed her chest further into his face, desperately spiraling toward completion.  Over and over she rose and fell, hands anchored to the seat on either side of his head, damp tendrils of hair clinging to her face.  The heat of their breaths and bodies was steaming up the car windows and creating a warm cocoon around them.

“Something’s happening Baby.”  His voice was a strangled whisper, his body was taught and straining.  “I feel you rippling all around me.  God it’s so tight.”

“Yes Jeff!  I’m going to-” she cried a second before her flushed torso bowed backwards in ecstasy.  Her rhythm began to falter, thighs trembling as another orgasm overtook her.  He felt her clamp down hard on him and then smaller pulses around his cock while she rode it out and it was just too intense.  His head slammed back against the seat as her release triggered his own.

“Ohmygod, ohgod, ohhhh...I can’t stop Baby,” he said frantically.  He came inside her, spurt after spurt and her spasming body took every last drop.  

When it subsided, his arms wrapped around her back and he pulled her flush against him, tucking her head into his shoulder while they both tried to calm their racing hearts and regulate their breathing.

 

*****

Bill almost thought she’d fallen asleep when a laugh bubbled out of her and she pulled back to look at him.

“What’s so funny Darlin’?” he asked Hillary.

“Oh, I was just thinking how Jeff and Diane’s first time was definitely a lot more pleasurable than mine, and probably yours.”

He chuckled.  “You can say that again.  A lot less awkward fumbling and a lot more stamina.  That was hot as hell Baby, thank you.”

“Happy Birthday Governor.”  She bit his earlobe then soothed it with her tongue.  “I hope it’s been memorable.  By the way, how’d you manage to get the detail to let you slip away to makeout point for the night?”

She could feel his shoulders shaking as he laughed.  “Look out the back window Hilly.”

She did, noticing the moonlight reflecting off two black sedans in the distance, headlights off.  

“Oh dear God William, you mean they’ve been here this whole time?  Knowing exactly what we were doing?”

Bill gave her a sheepish grin.  “Well not exactly.  They don’t know that Jeff and Diane were giving into their 1950s teenage desires, but I’m pretty sure they have a good idea what was happening in here. Get used to it Baby, if we get the Presidency, they’re no doubt going to witness a whole lot of stuff we might not want them to.”

Hillary smacked his shoulder playfully.  “You’re lucky I’ve been plied with bourbon and great sex, otherwise I might be angry with you.”  Her smile lit up the darkness.

Bill shifted and then groaned. “As much as I’d love to stay here with you forever Hilly, if I’m ever going to be able to walk again, I think we gotta get out of this backseat.  Mustangs were not built for tall people, and definitely not doing what we just did. Up!”

She pulled away and he slipped out of her with an audible groan.  “Easy for you Honey, all you have to do is pull up your pants, but Diane here has to get completely dressed.  Funny how that worked out.”

He gave her a wink.  “Can I help it if Jeff is one smooth fella?  Irresistible to his lady love?”  Hillary rolled her eyes as she started to gather up her clothes from the pile on the floor.

When they were both presentable, they climbed out of the backseat, patently avoiding eye contact with the Secret Service still parked behind them.

“Let’s blow this pop stand Diane,” Bill said as he revved the engine.  “Gotta get my Baby home by curfew.”

“I hope you’re going to make an honest woman out of me Jeff,” said Hillary.

“Steal your virtue and hit the road?  Never.  You’re mine for good.”

“Promise?” she asked.

“Promise.”

 

The end.

**Notes for the Chapter:**

> This is a gift for @royaltyisshe64, I hope I've done it justice :)


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